6 years ago
15:00

ShemaleZ

pain Is Her joy

Categories: bdsm, hd, pain

51 days ago
25:59

aShemaleTube

Sexy TV bound on bed, severely whipped, spanked with many instruments

Categories: bdsm, bed sex, bound, crop whip, domination, extreme, lingerie, pain, riding, slave

2 years ago
4:56

TrannyOne

Wife cuckolded by husband and trans maid Emma Rose

Categories: anal, assfucking, cheating, extreme, husband, lingerie, maid, pain, transsexual, uniform

7 years ago
5:24

aShemaleTube

Shemale Korra Del Rio Painful Anal

Categories: anal, blowjob, oral, pain, small tits, teen (18+), tranny, webcam

4 years ago
9:59

KeekAss

Smallish TRANSSEXUAL Honey Ella Hollywood Electrifies Nurse Cherie DeVille

Categories: big tits, blonde, blowjob, brunette, dick, fake tits, hd, pornstar, small tits, transsexual

Pornstars: Cherie Deville

3 years ago
6:56

HellPorno

Erotic nude anal with a TS slut on fire

Categories: anal, bdsm, blonde, blowjob, doggystyle, fetish, hardcore, pornstar, punishment, slut

7 years ago
12:19

TrannyOne

Intersexual creature screams and moans in amorous pain of anal sex

Categories: anal, blowjob, cute, moaning, pain, screaming, sucking, teen (18+)

2 years ago
6:16

TrannyOne

Crazy Wife Makes Her Husband To Have Sex With Trans Hooker

Categories: anal, ass, assfucking, crossdressing, hardcore, latina, slut, transsexual, transvestite, wife

2 years ago
15:32

KeekAss

Ash Steele - Mornings are a Ache in the Arse!

Categories: amateur, anal, ass, crossdressing, handjob, hardcore, hd, masturbation, pain, sissy

4 years ago
3:41

aShemaleTube

Sadistic Interracial Black Tgirls Fuck Live Webcam

Categories: amateur, black, ebony, homevideo, interracial, pain, teen (18+), tgirl, webcam

1 year ago
11:58

PornHub

rough anal fuck

Categories: amateur, anal, ass, extreme, gaping hole, small tits, solo, teen (18+), toys, transsexual

6 years ago
6:21

aShemaleTube

Pain and pleasure

Categories: big tits, blonde, blowjob, hd, jerking, oral, pain, sucking, transsexual

2 years ago
10:27

KeekAss

Vampire Roleplay Compiliation Movie Cyanide absorbes Synnz Aura

Categories: amateur, beauty, big tits, compilation, couple, dick, domination, goth, homevideo, seduce

2 years ago
6:57

KeekAss

Bashful She-Creature Pang Plumbed Sans A Condom

Categories: anal, asian, blowjob, brunette, condom, gaping hole, hd, ladyboy, pain, pov

8 months ago
1:12

aShemaleTube

Pain in the ass

Categories: amateur, anal, ass, big tits, brunette, homevideo, pain

2 years ago
31:02

xHamster

HUNG BLACK SHEMALE PAINFUL ANAL FUCK -SiNNe-

Categories: anal, big ass, big cock, big tits, black, domination, ebony, pain

2 years ago
2:09

TrannyOne

I Know You Love This Black, Ebony Stick Of Pain

Categories: anal, anus, ass, bdsm, black, blowjob, domination, ebony, hardcore, pain

3 years ago
6:05

KeekAss

Chinese Trans Honey Pang A Smashes Herself With A Fucktoy two

Categories: anal, asian, brunette, chinese, dildo, handjob, hd, jerking, masturbation, pain

2 years ago
5:01

TrannyOne

Tranny offers dick, white guy obliges.

Categories: anal, anus, ass, assfucking, big tits, blonde, blowjob, caught, extreme, pain

2 years ago
6:15

aShemaleTube

Skinny trans nanny takes care of the parent's needs too

Categories: anal, babysitter, cute, flexible, hardcore, hd, pain, skinny, transsexual

26 days ago
35:14

xHamster

Transsexual

Categories: amateur, anal, anal fisting, anal toying, close up, compilation, cumshot, fisting, hd, ladyboy

1 year ago
7:21

ShemaleZ

Blonde Sheshaft Painful Anal And Hot Facial

Categories: amateur, anal, blonde, cumshot, facial, pain, stockings

2 years ago
1:32

aShemaleTube

Sadistictranskitty KdamaGrey

Categories: amateur, pain

1 year ago
4:48

aShemaleTube

GAY BRAZIL AND SHEMALE ANAL PAIN GANG

Categories: amateur, anal, brazilian, gay, pain

23 days ago
9:51

KeekAss

Goddess Fucks a Slut Painfull on Fetish.

Categories: 3some, anal, bdsm, big ass, blonde, brunette, compilation, domination, femdom, fetish

54 days ago
2:34

xHamster

FTM fucking a huge dildo and pin orgasm

Categories: amateur, bdsm, big clit, gaping hole, hairy, hardcore, huge dildo, moaning, orgasm, pain

2 years ago
4:21

KeekAss

Putting toothpaste on my nasty t-stiffy and nutting rock-hard

Categories: amateur, beauty, big cock, cum, cumshot, dick, hd, masturbation, pain, pussy

2 years ago
6:14

TrannyOne

GENDER X Fucking my tranny friend for the first time! - Dante Colle, Ariel Demure

Categories: anal, anus, ass, assfucking, caught, crossdressing, extreme, first time, friend, pain

2 years ago
2:37

TrannyOne

DGB07 - EXTREME PIERCED FINALLY DEEP ANALFISTING PAIN SCREAM

Categories: anal, anus, ass, bdsm, booty, couple, extreme, fisting, pain, piercing

1 year ago
16:49

aShemaleTube

Ignore the shemale reaching out and screaming in pain and continue to fuck until she screams

Categories: big cock, crossdressing, ladyboy, pain, pornstar, screaming, small tits

Pornstars: Patricia Khan

7 years ago
7:25

TrannyOne

Brunette ladyboy Pang plays with his erect dong in bed

Categories: asian, bed sex, big tits, brunette, curly haired, hd, high heels, jerking, ladyboy, pain

1 year ago
0:20

xHamster

Sissy training Extreme CBT electric shock cock pain bdsm

Categories: amateur, bdsm, dick, dildo, domination, fisting, hd, huge cock, ladyboy, mistress

1 year ago
21:02

ShemaleMovie

Tranny, thai

Categories: asian, brunette, brutal, couple, ladyboy, pain, skinny, thai, tranny

2 months ago
23:11

XXXDan

Denise Humain in the bath, final hard self spanking and nipple pain

Categories: amateur, anal, bathroom, bdsm, compilation, crossdressing, dildo, fetish, german, hardcore

4 months ago
6:36

xHamster

Morning Procedures - bathing in sheer lingerie and painful anal stretching

Categories: amateur, anal, anal toying, bathroom, crossdressing, fantasy, german, hd, high heels, lingerie

2 months ago
10:04

Txxx

Doctor With Pain In Her Ass With Her Sexy Patients Cock With Gay Porn

Categories: amateur, ass, creampie, dick, doctor, fetish, gay, hd, lingerie, pain

2 months ago
7:03

xHamster

Maso Bitch Rebecca

Categories: austrian, bdsm, bitch, blonde, crossdressing, cum, cumshot, dick, european, hd

6 months ago
27:56

XXXDan

Pang-rum Thai Ladyboy pussy creampie

Categories: asian, babe, bbw, big ass, big cock, big tits, creampie, hardcore, ladyboy, pain

4 months ago
8:49

aShemaleTube

Shemale loves guy hard

Categories: hardcore, missionary, pain

6 months ago
5:28

ShemaleZ

My Patient Was Complaining Of Pain In His Leg, So I Treated Him With Ass Tea On The Table

Categories: amateur, ass, bdsm, big ass, big tits, compilation, cum in mouth, domination, fetish, interracial

20 days ago
8:01

xHamster

Transgender Pain Slut Strokes Off With Nipple Clamps For Whorish Reasons

Categories: bdsm, blonde, clamp, hd, ladyboy, masturbation, milf, nipples, pain, pretty

4 months ago
15:00

XoZilla

Shemale Spanked By The Sadistic Dude

Categories: anal, ass, asslick, big cock, big tits, blowjob, bondage, brunette, cowgirl, deep throat

6 months ago
29:52

ShemaleZ

Trans Girl Plays With An 18 Cm Dildo For The First Time Moans From Pain But Ends Up Liking It Succubo16

Categories: big ass, brunette, dildo, first time, hd, latina, moaning, pain, small tits, solo

3 months ago
5:59

HotMovs

Poor Slave Get Dominate To Sex By Sadistic Pervert Tranny - FemdomAustriaTs

Categories: cumshot, fetish, pain, slave, stockings, tranny

6 days ago
8:01

XXXDan

Transgender slut in pain jerks off with nipple clamps for lascivious reasons

Categories: bdsm, blonde, clamp, masturbation, milf, nipples, pain, slut, solo

3 months ago
6:23

aShemaleTube

Ladyboy feels pain in ass after giving nice blowjob

Categories: anal, asian, ass, ass to mouth, assfucking, barebacking, blowjob, hd, ladyboy, moaning

5 months ago
6:15

ShemaleZ

Geane Peron In The Pain In Male Ass Because Of Hard Shemale Dick

Categories: ass, barebacking, brazilian, dick, hd, latina, pain

3 months ago
24:23

ShemaleZ

Stacy Sadistic - Blonde Shemale Fucks And Creampies Chubby Girl

Categories: big cock, big tits, blonde, chubby, hd, pain, rimjob

34 days ago
10:35

aShemaleTube

No Pain, No Gain

Categories: blonde, cumshot, latina, pain

5 months ago
36:56

TrannyOne

Danni screaming on pain and pleasure

Categories: amateur, ass to mouth, barebacking, big cock, big tits, blonde, blowjob, hd, pain, screaming

3 months ago
6:27

aShemaleTube

Submissive ladyboy sucks and painfuly ass fucked

Categories: amateur, anal, asian, assfucking, blowjob, collar, doggystyle, hd, ladyboy, pain

3 months ago
6:00

HotMovs

Sadistic Tranny Torments Slaves Cock With A Stick - FemdomAustriaTs

Categories: bdsm, blowjob, cumshot, dick, lingerie, pain, slave, tranny

5 months ago
1:19

KeekAss

I make him perceive the ache

Categories: amateur, anal, ass to mouth, assfucking, barebacking, big cock, blonde, blowjob, bondage, hardcore

3 months ago
17:38

XXXDan

Self Bondage Pain Predicament - Sissy Maid Spiked Chastity Huge Dildo Ballet Boots

Categories: amateur, anal, ballerina, bdsm, beauty, big cock, bondage, boots, crossdressing, dildo

3 months ago
6:25

aShemaleTube

Ladyboy dick sucker gets painful anal

Categories: anal, asian, assfucking, barebacking, blowjob, dick, hd, ladyboy, pain, pov

2 months ago
2:38

XXXDan

Fagot Rebecca squirts in pain

Categories: bdsm, big ass, cumshot, lingerie, mature, nipples, pain, pantyhose, pissing, small tits

2 months ago
6:15

aShemaleTube

Cute big tits tranny hot masturbation after passion posing in lingerie

Categories: amateur, asian, big tits, cute, hd, ladyboy, lingerie, masturbation, pain, passionate

5 months ago
1:28

xHamster

PAINSLUT

Categories: bdsm, hd, pain, sissy, solo, stockings

2 months ago
6:27

XXXDan

Maso Muslima squirts in Pain

Categories: arab, bdsm, masturbation, mature, pain, pissing, small tits, solo, squirt

5 months ago
2:38

xHamster

Faggot Rebecca squirts in Pain

Categories: bdsm, big ass, cum, cumshot, hd, mature, nipples, pain, pantyhose, sissy

5 months ago
7:05

aShemaleTube

Redhead Asian shemale all covered in pain gets fucked doggystyle till facial

Categories: amateur, asian, cumshot, doggystyle, facial, ladyboy, pain, redhead, teen (18+)

4 months ago
8:37

xHamster

Black blow up spiked butt plug for my S&M Daddies!

Categories: amateur, american, anal, bbw, bdsm, beauty, black, buttplug, crossdressing, daddies

4 months ago
19:03

KeekAss

Stringing up Wedgie Fetish - Frontal Wedgie puts strain on my poon - Rips My Undies to Shreds!

Categories: amateur, boy, clit, dirty, fetish, hd, masturbation, pain, panties, pussy

4 months ago
10:28

aShemaleTube

Gold Predator BBC Brutally Destroys White Sluts Hole & Makes Me Scream

Categories: anal, big black cock, hd, model, pain, pornstar, screaming, sissy, slut, transsexual

Pornstars: Candy Ass

21 days ago
2:05

aShemaleTube

1 painful bang session tranny huge rod bang a dude aaii

Categories: amateur, pain, tranny

19 days ago
6:23

AnalDin

Ladyboy feels pain in booty after giving nice giving head

Categories: anal, asian, ass, assfucking, barebacking, blowjob, booty, giving head, ladyboy, oral

50 days ago
11:32

xHamster

Sissy faggot bitch

Categories: amateur, anal, bitch, crossdressing, danish, dildo, emo, hd, lingerie, pain

7 months ago
6:02

xHamster

Horny sissy pushes dildo into his asshole with less lubricant and gets pain and pleasure at the same time..

Categories: amateur, anal, anal toying, ass, crossdressing, dildo, femboy, gay, hd, pain

6 months ago
5:08

KeekAss

Shemale is a flawless dicksucker

Categories: anal, ass, barebacking, big black cock, blowjob, brunette, dick, hd, ladyboy, masturbation

7 months ago
0:43

xHamster

Painful constant wanking after chastity phase! Tranny Girl has 9 (!) ruined orgasms and 5 cumshots!!

Categories: big tits, blonde, cum, cumshot, domination, fetish, german, hd, masturbation, orgasm

6 months ago
5:07

KeekAss

Transgender Princess cutie in a fantastic act

Categories: anal, big ass, big tits, blowjob, brunette, cute, fantasy, hd, husband, lingerie

7 months ago
4:28

ShemaleZ

Painful Anal Stretching And Outdoor Cumshot

Categories: amateur, anal, cumshot, hd, lingerie, mature, outdoor, pain, redhead, solo

3 days ago
6:06

PornHub

Naked Trans Yoga! For Back Pain

Categories: 18 year old, amateur, big cock, big tits, brunette, cute, feet, fetish, nude, old

6 months ago
15:59

HClips

Pain Slut Dee with her swinging weights

Categories: amateur, bdsm, milf, pain, slut, swinger

7 months ago
5:18

aShemaleTube

thin tranny likes pain with pleasure

Categories: pain, solo, thin, tranny, webcam

7 months ago
5:11

xHamster

Masochistic tranny whips himself with flogger

Categories: amateur, american, bdsm, big ass, fetish, hardcore, hd, homevideo, ladyboy, pain

8 months ago
5:07

KeekAss

Rigid gang-hookup for raw shemale

Categories: anal, blonde, hardcore, hd, interracial, ladyboy, pain, pawg, riding, slim

8 months ago
5:52

UPornia

Anal Pain

Categories: 3some, anal, big tits, blonde, cumshot, pain

7 months ago
6:19

xHamster

Sexy sissy slut rides huge dildo beside the wash basin, gets it fully inside her ass pussy and moans loudly!

Categories: amateur, anal, ass, crossdressing, dildo, extreme, gay, hardcore, hd, huge dildo

7 months ago
5:07

KeekAss

Bootie screw for t-girl untill climax

Categories: anal, ass, blowjob, brunette, hardcore, hd, ladyboy, orgasm, pain, slut

7 months ago
8:19

xHamster

Horny sissy rides dildo like a porn star and moans in ecstasy and pain!

Categories: anal, anal toying, crossdressing, dildo, extreme, gay, hardcore, hd, huge dildo, indian

7 months ago
6:14

aShemaleTube

The pain in male ass because of hard shemale dick

Categories: anal, ass, assfucking, barebacking, big cock, blowjob, brazilian, deep throat, dick, hd

7 months ago
25:51

ShemaleZ

The Boys Ass Was Destroyed Successfully He Is Screaming In Pain

Categories: ass, big ass, big cock, big tits, boy, brunette, handjob, pain, screaming, tattoo

1 year ago
19:12

HDSex

Unexperienced, san-diego, big-tits

Categories: amateur, american, anal, big tits, brutal, college, desk, homevideo, pain

1 year ago
42:25

ShemaleZ

Driver S Ed-ache - Whitney Wright And Erica Cherry

Categories: big cock, handjob, hd, lingerie, milf, pain, redhead

13 days ago
5:24

JizzBunker

MissRose TS - Rosanna IN PRIVATE - WILD SHEMALE, painful MASTURBATION - Rough ass, big SHAKE - cumshot

Categories: anal, ass, beauty, big ass, big cock, blonde, creampie, cumshot, facial, hardcore

1 year ago
6:40

ShemaleZ

Mistress Cy Ipl Painful Hair Removal

Categories: amateur, big ass, big tits, hd, milf, mistress, pain, small tits, tattoo

11 months ago
6:11

FlyFlv

Busty Trans Needs Her Hole Filled

Categories: anal, big tits, blonde, dick, feet, lesbian, lingerie, missionary, orgasm, pain

31 days ago
5:18

HDSex

Intense ebony kink mesh with Ariel X and Mr. Pete

Categories: bdsm, bizarre, bondage, domination, ebony, exhibitionist, group sex, hardcore, humiliation, kinky

6 months ago
5:52

xHamster

Sissy fox Ranjini moans while riding dildo like a porn star wearing a sexy thong!!!

Categories: amateur, anal, crossdressing, dildo, extreme, femboy, gay, hardcore, hd, indian

6 months ago
5:07

KeekAss

Rock Hard rod for a frolic transgender princess

Categories: anal, ass, big ass, big cock, big tits, brunette, dick, hd, pain, pornstar

Pornstars: Alexis Texas

1 year ago
17:31

ShemaleZ

Stacy Sadistic And Jenna Jaden - Ts Getting Fucked By Dominant Trans

Categories: blonde, fetish, hd, pain, tattoo, transsexual

56 days ago
1:19

xHamster

sissy slut with nipple clamps

Categories: amateur, boots, british, clamp, crossdressing, fishnet, hd, lingerie, mature, nipples

7 months ago
3:26

ShemaleZ

Dolly Sucks A Pain Slut While His Nipples Are Clamped And Weighted 4 Min

Categories: amateur, blonde, clamp, doll, hd, mature, nipples, pain, slut, sucking

6 months ago
6:02

KeekAss

Maria Flavia hard-core ass-fuck lovemaking

Categories: amateur, anal, assfucking, brazilian, brunette, hardcore, hd, latina, masturbation, pain

7 days ago
5:41

JizzBunker

Sadistic vampire Mistress

Categories: amateur, bdsm, big ass, chubby, crossdressing, fetish, hardcore, mistress, pain, solo

1 year ago
3:00

PornHub

Dare: Intense Nipple Pinching and Pulling

Categories: amateur, clamp, crossdressing, dare, fetish, hardcore, kinky, moaning, nipples, pain

8 months ago
1:30

PornHub

Hot Sauce on Clit pt 2/3

Categories: amateur, big clit, boy, clit, femboy, hardcore, pain, pussy, reality, rough

6 months ago
5:07

KeekAss

Transgender Princess's ass gets ruined

Categories: anal, ass, big ass, blowjob, brunette, contest, crazy, cumshot, hd, interracial

1 year ago
16:11

ShemaleZ

Ass To Mouth: Painful Naked Anal Dildo Masturbation

Categories: amateur, american, anal toying, ass to mouth, big ass, brunette, masturbation, nude, pain, solo

1 year ago
12:58

PornHub

Sissy Destroys Balls and Cums!

Categories: amateur, ball busting, balls, bdsm, bondage, clothed sex, crossdressing, cum, cumshot, dick

1 year ago
11:34

PornHub

Fit Trans Beauties Go Bareback After A Gym Workout

Categories: amateur, ass, babe, beauty, big ass, big cock, big tits, blowjob, gym, pain

1 year ago
10:01

KeekAss

Working on Sissy Sub Denise Humain Puffies for hours Part 1

Categories: amateur, bdsm, bondage, brunette, crossdressing, domination, fetish, hd, ladyboy, lingerie

1 year ago
6:07

ShemaleZ

Young Goth Trans Does Painful Anal

Categories: amateur, american, anal, big ass, goth, hd, pain, solo, teen (18+), toys

10 months ago
6:13

FlyFlv

Massage Session Goes Wild As Trannies Get Out Of Control

Categories: anal, assfingering, big cock, blonde, blowjob, brunette, lesbian, massage, pain, tattoo

1 year ago
7:50

aShemaleTube

blonde sheshaft painful anal and hot facial

Categories: amateur, anal, blonde, facial, pain

1 year ago
27:57

ShemaleZ

Trans Bbw Madame With Stacy Sadistic, Morgan P And Madame Morgan

Categories: bbw, big ass, brunette, cumshot, milf, pain, transsexual

1 year ago
18:34

aShemaleTube

Kiss, pain, and intimate moments

Categories: crossdressing, domination, fat, hd, kissing, latex, mature, pain

10 months ago
7:39

KeekAss

Excruciating Nip Climax

Categories: amateur, blonde, crossdressing, cumshot, hd, homevideo, masturbation, mature, nipples, orgasm

5 months ago
13:59

xHamster

Let her feel what Nipple Pain means. Let her suffer to her limit while we smile at her.

Categories: abuse, amateur, bdsm, crossdressing, crying, domination, fetish, german, hardcore, hd

10 months ago
8:45

xHamster

Beautiful sissy pleasures herself with nipple clamps, nettles and a dildo, then makes herself cum with her vibrator

Categories: anal, anal toying, ass, bdsm, beauty, big cock, clamp, crossdressing, cum, cumshot

1 year ago
4:52

PornHub

JUDE LYNX — “DO YOU LIKE A FTM WET PUSSY IN HEAT?”

Categories: amateur, babe, blonde, caught, college, cum, cumshot, denial, female orgasm, femboy

10 months ago
1:39

PornHub

Painful cum cage breaks

Categories: amateur, bdsm, cage, cum, cumshot, masturbation, pain, sissy, solo, transsexual

1 year ago
3:58

PornHub

Sexy Trans Girl Drips Hot Wax On Herself (1 of 3) The Wax

Categories: amateur, babe, blonde, fetish, kinky, moaning, pain, sadomasochism, solo, transsexual

1 year ago
4:53

ShemaleZ

Thin Shemale Likes Pain With Pleasure

Categories: amateur, blonde, lingerie, pain, solo, stockings, thin, toys, webcam

1 year ago
0:54

aShemaleTube

Insane huge dildo - Part 5 (painful fart)

Categories: amateur, anal, farting, fetish, huge dildo, pain, sissy, stockings, toys

1 year ago
5:10

HDSex

Jerk, trans camgirl, asshole fetish

Categories: ass, fetish, masturbation, pain, toys, transsexual, webcam

9 months ago
5:55

PornGem

Three Cum Shots - Two From Thick TS Cock Fucking His Ass

Categories: anal, ass, big cock, black, blindfolded, blonde, blowjob, bondage, cumshot, dick

11 months ago
11:58

KeekAss

tough ass-fuck drill

Categories: amateur, anal, anal fisting, anal toying, ass, assfucking, big black cock, extreme, farting, first time

9 months ago
4:37

ShemaleZ

Tranny Tranny Pang Likes Toying Her Butt

Categories: asian, ass, big ass, big tits, ladyboy, pain, redhead, solo, toys, tranny